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In the title compound, [Ni(C9H10NO3)(C6H18N4)]I·2H2O, the NiII atom is in a slightly distorted octa­hedral coordination environment. In the crystal structure, extensive hydrogen bonding links mol­ecules into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602366X/lh2102sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602366X/lh2102Isup2.hkl
Contains datablock I

CCDC reference: 613778

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.037
  • wR factor = 0.106
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT395_ALERT_2_C Deviating X-O-Y Angle from 120 Deg for O5 140.60 Deg. PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2C ... ? PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2D ... ? PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3D ... ? PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4D ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.49 From the CIF: _reflns_number_total 4255 Count of symmetry unique reflns 2589 Completeness (_total/calc) 164.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1666 Fraction of Friedel pairs measured 0.643 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
[Ni(C9H10NO3)(C6H18N4)]I·2H2OF(000) = 556
Mr = 548.05Dx = 1.703 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4464 reflections
a = 10.2197 (14) Åθ = 2.6–28.2°
b = 10.3097 (14) ŵ = 2.39 mm1
c = 10.2801 (14) ÅT = 293 K
β = 99.415 (2)°Block, purple
V = 1068.5 (3) Å30.20 × 0.20 × 0.10 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
4255 independent reflections
Radiation source: fine-focus sealed tube4056 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
φ and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1213
Tmin = 0.647, Tmax = 0.796k = 1013
6707 measured reflectionsl = 1311
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.065P)2 + 0.0892P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
4255 reflectionsΔρmax = 0.74 e Å3
244 parametersΔρmin = 0.67 e Å3
2 restraintsAbsolute structure: Flack (1983), 1697 Friedels
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (2)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.26927 (5)1.06628 (6)0.24592 (5)0.02964 (13)
I10.21287 (4)0.43376 (4)0.91397 (4)0.05732 (14)
O10.4456 (3)1.0168 (4)0.3690 (3)0.0416 (7)
O20.5898 (4)1.0844 (5)0.5396 (4)0.0551 (10)
O30.0539 (4)0.6947 (4)0.6322 (4)0.0506 (9)
H30.10410.63230.63600.076*
N10.2786 (3)0.9254 (5)0.1028 (3)0.0370 (8)
N20.1702 (4)0.9144 (4)0.3327 (4)0.0428 (9)
H2C0.21270.89920.41500.051*
H2D0.08700.93970.33810.051*
N30.1003 (4)1.1301 (4)0.1179 (4)0.0385 (8)
H3C0.02651.10450.14780.046*
H3D0.09991.21730.11310.046*
N40.3977 (4)1.1669 (5)0.1335 (4)0.0449 (10)
H4C0.35991.24230.10350.054*
H4D0.47511.18520.18570.054*
N50.2647 (4)1.1973 (4)0.3988 (4)0.0371 (8)
H5C0.25831.27820.36560.045*
H5D0.19191.18220.43530.045*
C10.1655 (6)0.7944 (6)0.2555 (5)0.0502 (12)
H1A0.08020.78670.19870.060*
H1B0.17700.72000.31400.060*
C20.2749 (6)0.7984 (6)0.1737 (5)0.0473 (11)
H2A0.35940.78460.23040.057*
H2B0.26220.72850.10960.057*
C30.1595 (5)0.9363 (6)0.0012 (4)0.0446 (10)
H3A0.09160.87750.01920.053*
H3B0.18280.91010.08510.053*
C40.1035 (5)1.0739 (7)0.0136 (5)0.0487 (12)
H4A0.15801.12760.06070.058*
H4B0.01441.07220.06370.058*
C50.4051 (5)0.9487 (6)0.0541 (6)0.0527 (13)
H5A0.40710.89660.02410.063*
H5B0.47820.92150.12080.063*
C60.4229 (6)1.0879 (7)0.0218 (6)0.0532 (14)
H6A0.51251.10250.00540.064*
H6B0.36161.11150.05690.064*
C70.4807 (4)1.0871 (5)0.4676 (4)0.0358 (9)
C80.3820 (5)1.1894 (5)0.5015 (4)0.0396 (10)
H8A0.42681.27360.50380.048*
C90.3485 (6)1.1655 (5)0.6406 (5)0.0451 (11)
H9A0.43021.16280.70370.054*
H9B0.29581.23730.66430.054*
C100.2718 (5)1.0380 (5)0.6490 (4)0.0371 (10)
C110.3353 (4)0.9203 (5)0.6617 (4)0.0338 (8)
H11A0.42740.91770.67280.041*
C120.2649 (5)0.8055 (5)0.6584 (4)0.0373 (9)
H12A0.30940.72640.66650.045*
C130.1276 (5)0.8089 (5)0.6429 (4)0.0374 (10)
C140.0613 (4)0.9259 (6)0.6370 (4)0.0424 (10)
H14A0.03050.92840.63080.051*
C150.1348 (5)1.0403 (5)0.6404 (5)0.0431 (12)
H15A0.09111.11970.63680.052*
O40.2049 (5)0.4940 (4)0.5802 (4)0.0564 (10)
H4OA0.26570.52080.54440.085*
H4OB0.23410.46750.65450.085*
O50.7199 (8)0.9431 (6)0.7423 (4)0.107 (3)
H5OA0.73570.94160.82410.160*
H5OB0.68040.98640.68170.160*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0288 (2)0.0321 (3)0.0276 (2)0.0021 (2)0.00359 (18)0.0005 (2)
I10.0486 (2)0.0680 (3)0.0562 (2)0.00771 (17)0.01125 (15)0.00765 (18)
O10.0394 (17)0.0468 (19)0.0370 (16)0.0141 (14)0.0010 (13)0.0006 (13)
O20.0395 (19)0.081 (3)0.0413 (18)0.0081 (19)0.0041 (14)0.0021 (19)
O30.0383 (18)0.050 (2)0.065 (2)0.0106 (16)0.0132 (16)0.0073 (18)
N10.0344 (17)0.044 (2)0.0323 (16)0.0012 (17)0.0034 (13)0.0068 (17)
N20.051 (2)0.043 (2)0.0369 (18)0.0098 (19)0.0126 (16)0.0008 (16)
N30.0279 (17)0.037 (2)0.049 (2)0.0047 (15)0.0015 (15)0.0019 (16)
N40.037 (2)0.052 (3)0.045 (2)0.0036 (19)0.0077 (17)0.0077 (18)
N50.045 (2)0.033 (2)0.0337 (18)0.0060 (16)0.0093 (15)0.0015 (14)
C10.063 (3)0.035 (3)0.049 (3)0.013 (2)0.000 (2)0.001 (2)
C20.052 (3)0.037 (3)0.052 (3)0.004 (2)0.003 (2)0.003 (2)
C30.048 (2)0.051 (3)0.032 (2)0.005 (3)0.0010 (18)0.004 (2)
C40.044 (2)0.065 (3)0.035 (2)0.003 (3)0.0005 (18)0.010 (2)
C50.046 (3)0.062 (4)0.056 (3)0.011 (3)0.022 (2)0.002 (3)
C60.044 (3)0.070 (4)0.049 (3)0.006 (3)0.020 (2)0.003 (2)
C70.035 (2)0.039 (3)0.034 (2)0.0020 (18)0.0059 (17)0.0099 (17)
C80.046 (2)0.040 (3)0.033 (2)0.013 (2)0.0062 (18)0.0025 (18)
C90.064 (3)0.040 (3)0.032 (2)0.014 (2)0.009 (2)0.0080 (18)
C100.043 (2)0.043 (3)0.0243 (18)0.0006 (19)0.0050 (17)0.0003 (16)
C110.0271 (17)0.035 (2)0.0388 (19)0.0011 (18)0.0045 (15)0.0024 (18)
C120.037 (2)0.036 (2)0.040 (2)0.0048 (19)0.0082 (18)0.0035 (18)
C130.032 (2)0.048 (3)0.032 (2)0.012 (2)0.0058 (16)0.0051 (19)
C140.032 (2)0.056 (3)0.041 (2)0.010 (2)0.0113 (17)0.010 (2)
C150.045 (3)0.049 (3)0.038 (2)0.019 (2)0.014 (2)0.0069 (19)
O40.057 (2)0.058 (3)0.052 (2)0.0026 (19)0.0043 (18)0.0006 (18)
O50.200 (8)0.058 (3)0.052 (3)0.040 (5)0.010 (3)0.001 (3)
Geometric parameters (Å, º) top
Ni1—N52.079 (4)C3—C41.527 (9)
Ni1—N12.081 (4)C3—H3A0.9700
Ni1—O12.089 (3)C3—H3B0.9700
Ni1—N32.099 (4)C4—H4A0.9700
Ni1—N22.138 (4)C4—H4B0.9700
Ni1—N42.153 (4)C5—C61.490 (9)
O1—C71.250 (6)C5—H5A0.9700
O2—C71.233 (6)C5—H5B0.9700
O3—C131.393 (6)C6—H6A0.9700
O3—H30.8200C6—H6B0.9700
N1—C51.480 (6)C7—C81.538 (7)
N1—C31.487 (6)C8—C91.543 (6)
N1—C21.502 (7)C8—H8A0.9800
N2—C11.465 (7)C9—C101.540 (7)
N2—H2C0.9000C9—H9A0.9700
N2—H2D0.9000C9—H9B0.9700
N3—C41.476 (7)C10—C111.372 (7)
N3—H3C0.9000C10—C151.389 (7)
N3—H3D0.9000C11—C121.383 (7)
N4—C61.464 (7)C11—H11A0.9300
N4—H4C0.9000C12—C131.386 (7)
N4—H4D0.9000C12—H12A0.9300
N5—C81.464 (6)C13—C141.380 (8)
N5—H5C0.9000C14—C151.396 (8)
N5—H5D0.9000C14—H14A0.9300
C1—C21.506 (8)C15—H15A0.9300
C1—H1A0.9700O4—H4OA0.8200
C1—H1B0.9700O4—H4OB0.8200
C2—H2A0.9700O5—H5OA0.8301
C2—H2B0.9700O5—H5OB0.8177
N5—Ni1—N1176.00 (17)N1—C3—C4112.4 (4)
N5—Ni1—O179.89 (15)N1—C3—H3A109.1
N1—Ni1—O197.09 (14)C4—C3—H3A109.1
N5—Ni1—N398.77 (16)N1—C3—H3B109.1
N1—Ni1—N384.46 (16)C4—C3—H3B109.1
O1—Ni1—N3175.16 (17)H3A—C3—H3B107.9
N5—Ni1—N295.16 (16)N3—C4—C3110.7 (4)
N1—Ni1—N282.13 (16)N3—C4—H4A109.5
O1—Ni1—N289.36 (16)C3—C4—H4A109.5
N3—Ni1—N295.40 (17)N3—C4—H4B109.5
N5—Ni1—N4100.60 (17)C3—C4—H4B109.5
N1—Ni1—N481.62 (17)H4A—C4—H4B108.1
O1—Ni1—N484.36 (16)N1—C5—C6112.1 (5)
N3—Ni1—N491.34 (17)N1—C5—H5A109.2
N2—Ni1—N4161.70 (18)C6—C5—H5A109.2
C7—O1—Ni1117.0 (3)N1—C5—H5B109.2
C13—O3—H3109.5C6—C5—H5B109.2
C5—N1—C3113.7 (4)H5A—C5—H5B107.9
C5—N1—C2113.4 (4)N4—C6—C5108.5 (4)
C3—N1—C2109.4 (4)N4—C6—H6A110.0
C5—N1—Ni1105.6 (3)C5—C6—H6A110.0
C3—N1—Ni1109.2 (3)N4—C6—H6B110.0
C2—N1—Ni1104.9 (3)C5—C6—H6B110.0
C1—N2—Ni1111.6 (3)H6A—C6—H6B108.4
C1—N2—H2C109.3O2—C7—O1125.8 (5)
Ni1—N2—H2C109.3O2—C7—C8116.2 (4)
C1—N2—H2D109.3O1—C7—C8118.0 (4)
Ni1—N2—H2D109.3N5—C8—C7111.4 (4)
H2C—N2—H2D108.0N5—C8—C9113.4 (4)
C4—N3—Ni1108.2 (3)C7—C8—C9110.7 (4)
C4—N3—H3C110.1N5—C8—H8A107.0
Ni1—N3—H3C110.1C7—C8—H8A107.0
C4—N3—H3D110.1C9—C8—H8A107.0
Ni1—N3—H3D110.1C10—C9—C8112.3 (4)
H3C—N3—H3D108.4C10—C9—H9A109.1
C6—N4—Ni1110.7 (3)C8—C9—H9A109.1
C6—N4—H4C109.5C10—C9—H9B109.1
Ni1—N4—H4C109.5C8—C9—H9B109.1
C6—N4—H4D109.5H9A—C9—H9B107.9
Ni1—N4—H4D109.5C11—C10—C15118.5 (5)
H4C—N4—H4D108.1C11—C10—C9121.5 (5)
C8—N5—Ni1113.1 (3)C15—C10—C9120.0 (5)
C8—N5—H5C109.0C10—C11—C12121.3 (4)
Ni1—N5—H5C109.0C10—C11—H11A119.4
C8—N5—H5D109.0C12—C11—H11A119.4
Ni1—N5—H5D109.0C11—C12—C13119.6 (5)
H5C—N5—H5D107.8C11—C12—H12A120.2
N2—C1—C2108.5 (4)C13—C12—H12A120.2
N2—C1—H1A110.0C14—C13—C12120.5 (5)
C2—C1—H1A110.0C14—C13—O3118.7 (4)
N2—C1—H1B110.0C12—C13—O3120.8 (5)
C2—C1—H1B110.0C13—C14—C15118.6 (4)
H1A—C1—H1B108.4C13—C14—H14A120.7
N1—C2—C1112.0 (4)C15—C14—H14A120.7
N1—C2—H2A109.2C10—C15—C14121.4 (5)
C1—C2—H2A109.2C10—C15—H15A119.3
N1—C2—H2B109.2C14—C15—H15A119.3
C1—C2—H2B109.2H4OA—O4—H4OB110.1
H2A—C2—H2B107.9H5OA—O5—H5OB140.6
N5—Ni1—O1—C76.6 (3)C3—N1—C2—C168.8 (5)
N1—Ni1—O1—C7176.0 (3)Ni1—N1—C2—C148.3 (4)
N2—Ni1—O1—C7102.0 (3)N2—C1—C2—N147.6 (6)
N4—Ni1—O1—C795.2 (4)C5—N1—C3—C490.3 (5)
O1—Ni1—N1—C558.2 (3)C2—N1—C3—C4141.8 (4)
N3—Ni1—N1—C5117.2 (3)Ni1—N1—C3—C427.4 (5)
N2—Ni1—N1—C5146.6 (3)Ni1—N3—C4—C336.7 (5)
N4—Ni1—N1—C525.0 (3)N1—C3—C4—N343.7 (6)
O1—Ni1—N1—C3179.1 (3)C3—N1—C5—C671.5 (6)
N3—Ni1—N1—C35.5 (3)C2—N1—C5—C6162.6 (4)
N2—Ni1—N1—C390.8 (3)Ni1—N1—C5—C648.2 (5)
N4—Ni1—N1—C397.7 (3)Ni1—N4—C6—C525.1 (5)
O1—Ni1—N1—C261.9 (3)N1—C5—C6—N449.6 (6)
N3—Ni1—N1—C2122.7 (3)Ni1—O1—C7—O2168.8 (4)
N2—Ni1—N1—C226.5 (3)Ni1—O1—C7—C89.3 (5)
N4—Ni1—N1—C2145.1 (3)Ni1—N5—C8—C71.3 (5)
N5—Ni1—N2—C1174.4 (4)Ni1—N5—C8—C9124.4 (4)
N1—Ni1—N2—C12.6 (4)O2—C7—C8—N5171.3 (4)
O1—Ni1—N2—C194.6 (4)O1—C7—C8—N57.0 (6)
N3—Ni1—N2—C186.3 (4)O2—C7—C8—C961.5 (5)
N4—Ni1—N2—C124.9 (7)O1—C7—C8—C9120.2 (4)
N5—Ni1—N3—C4164.9 (4)N5—C8—C9—C1059.8 (6)
N1—Ni1—N3—C417.5 (4)C7—C8—C9—C1066.3 (6)
N2—Ni1—N3—C499.0 (4)C8—C9—C10—C1179.6 (6)
N4—Ni1—N3—C464.0 (4)C8—C9—C10—C1598.8 (6)
N5—Ni1—N4—C6176.6 (3)C15—C10—C11—C123.8 (6)
N1—Ni1—N4—C60.1 (4)C9—C10—C11—C12174.6 (4)
O1—Ni1—N4—C698.0 (4)C10—C11—C12—C130.5 (6)
N3—Ni1—N4—C684.3 (4)C11—C12—C13—C143.0 (7)
N2—Ni1—N4—C627.5 (7)C11—C12—C13—O3176.6 (4)
O1—Ni1—N5—C82.3 (3)C12—C13—C14—C153.1 (6)
N3—Ni1—N5—C8173.0 (3)O3—C13—C14—C15176.5 (4)
N2—Ni1—N5—C890.7 (3)C11—C10—C15—C143.7 (7)
N4—Ni1—N5—C880.0 (3)C9—C10—C15—C14174.8 (4)
Ni1—N2—C1—C222.3 (5)C13—C14—C15—C100.3 (7)
C5—N1—C2—C1163.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4OB···I10.822.733.475 (4)151
O3—H3···O40.821.902.687 (6)160
O5—H5OB···O20.821.892.707 (6)179
N5—H5D···O3i0.902.503.219 (6)138
N5—H5C···O5ii0.902.062.937 (7)164
N4—H4C···I1iii0.903.003.851 (5)159
N3—H3C···I1i0.903.003.756 (4)143
O5—H5OA···I1iv0.832.663.489 (4)179
O4—H4OA···O2v0.821.942.762 (6)180
N2—H2C···Cg10.902.433.210 (4)144
C3—H3B···Cg20.972.783.695 (5)158
Symmetry codes: (i) x, y+1/2, z+1; (ii) x+1, y+1/2, z+1; (iii) x, y+1, z1; (iv) x+1, y+1/2, z+2; (v) x+1, y1/2, z+1.
 

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